Spiro compound and organic light-emitting device comprising same

ABSTRACT

The present specification relates to a spiro structure compound and an organic light emitting device including the same.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a national phase entry under 35 U.S.C. § 371of International Application No. PCT/KR2016/011184 filed Oct. 6, 2016,which claims priority from Korean Patent Application No. 10-2015-0140423filed Oct. 6, 2015 and Korean Patent Application No. 10-2016-0071248filed Jun. 8, 2016, all of which are incorporated herein by reference.

TECHNICAL FIELD

The present specification relates to a spiro structure compound and anorganic light emitting device including the same.

BACKGROUND ART

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy by using anorganic material. An organic light emitting device using the organiclight emitting phenomenon usually has a structure including a positiveelectrode, a negative electrode, and an organic material layerinterposed therebetween. Here, the organic material layer may have amulti-layered structure composed of different materials in order toimprove the efficiency and stability of an organic light emitting devicein many cases, and for example, may be composed of a hole injectionlayer, a hole transport layer, a light emitting layer, an electrontransport layer, an electron injection layer, and the like. In thestructure of the organic light emitting device, if a voltage is appliedbetween two electrodes, holes are injected from a positive electrodeinto the organic material layer and electrons are injected from anegative electrode into the organic material layer, and when theinjected holes and electrons meet each other, an exciton is formed, andlight is emitted when the exciton falls down again to a ground state.

There is a continuous need for developing a new material for theaforementioned organic light emitting device.

CITATION LIST Patent Document

International Publication No. 2003-012890

DISCLOSURE Technical Problem

The present specification provides a spiro structure compound and anorganic light emitting device including the same.

Technical Solution

An exemplary embodiment of the present specification provides a compoundrepresented by the following Chemical Formula 1.

In Chemical Formula 1,

X1 is O or S, and

any one of R1 to R12 is the following Chemical Formula B, and the othersand R13 to R16 are the same as or different from each other, and areeach independently hydrogen; deuterium; a nitrile group; a nitro group;a hydroxy group; a carbonyl group; an ester group; an imide group; anamide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted amine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group,

In Chemical Formula B,

L1 is a direct bond; a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group, and

Ar1 and Ar2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group, or combine with eachother to form a substituted or unsubstituted ring.

Further, an exemplary embodiment of the present specification providesan organic light emitting device including: a first electrode; a secondelectrode provided to face the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, in which one or more layers of the organic material layersinclude the spiro structure compound represented by Chemical Formula 1.

Advantageous Effects

A spiro structure compound according to an exemplary embodiment of thepresent specification may be used as a material for an organic materiallayer of an organic light emitting device, and it is possible to improveefficiency, achieve low driving voltage, and/or improve lifetimecharacteristics in the organic light emitting device by using the same.

DESCRIPTION OF DRAWINGS

FIG. 1 illustrates an organic light emitting device 10 according to anexemplary embodiment of the present specification.

FIG. 2 illustrates an organic light emitting device 11 according toanother exemplary embodiment of the present specification.

MODE FOR INVENTION

Hereinafter, the present specification will be described in more detail.

The present specification provides the spiro structure compoundrepresented by Chemical Formula 1.

When one part “includes” one constituent element in the presentspecification, unless otherwise specifically described, this does notmean that another constituent element is excluded, but means thatanother constituent element may be further included.

When one member is disposed “on” another member in the presentspecification, this includes not only a case where the one member isbrought into contact with the another member, but also a case wherestill another member is present between the two members.

In the present specification, examples of the substituents will bedescribed below, but the present specification is not limited thereto.

The term “substitution” means that a hydrogen atom bonded to a carbonatom of a compound is changed into another substituent, and a positionto be substituted is not limited as long as the position is a positionat which the hydrogen atom is substituted, that is, a position at whichthe substituent may be substituted, and when two or more aresubstituted, the two or more substituents may be the same as ordifferent from each other.

In the present specification, the term “substituted or unsubstituted”means being substituted with one or two or more substituents selectedfrom the group consisting of deuterium; a halogen group; a nitrilegroup; a nitro group; an imide group; an amide group; a carbonyl group;an ester group; a hydroxy group; a substituted or unsubstituted alkylgroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted alkoxy group; a substituted or unsubstituted aryloxygroup; a substituted or unsubstituted alkylthioxy group; a substitutedor unsubstituted arylthioxy group; a substituted or unsubstitutedalkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted silyl group; a substituted or unsubstituted boron group; asubstituted or unsubstituted amine group; a substituted or unsubstitutedarylphosphine group; a substituted or unsubstituted phosphine oxidegroup; a substituted or unsubstituted aryl group; and a substituted orunsubstituted heterocyclic group or being substituted with a substituentto which two or more substituents are linked among the substituentsexemplified above, or having no substituent. For example, “thesubstituent to which two or more substituents are linked” may be abiphenyl group. That is, the biphenyl group may also be an aryl group,and may be interpreted as a substituent to which two phenyl groups arelinked.

In the present specification,

means a moiety bonded to another substituent or a binding portion.

In the present specification, the halogen group may be fluorine,chlorine, bromine, or iodine.

In the present specification, the number of carbon atoms of an imidegroup is not particularly limited, but is preferably 1 to 30.Specifically, the imide group may be a compound having the followingstructures, but is not limited thereto.

In the present specification, for an amide group, the nitrogen of theamide group may be substituted with hydrogen, a straight-chained,branch-chained, or cyclic alkyl group having 1 to 30 carbon atoms, or anaryl group having 6 to 30 carbon atoms. Specifically, the amide groupmay be a compound having the following structural formulae, but is notlimited thereto.

In the present specification, the number of carbon atoms of a carbonylgroup is not particularly limited, but is preferably 1 to 30.Specifically, the carbonyl group may be a compound having the followingstructures, but is not limited thereto.

In the present specification, for an ester group, the oxygen of theester group may be substituted with a straight-chained, branch-chained,or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl grouphaving 6 to 30 carbon atoms. Specifically, the ester group may be acompound having the following structural formulae, but is not limitedthereto.

In the present specification, the alkyl group may be straight-chained orbranch-chained, and the number of carbon atoms thereof is notparticularly limited, but is preferably 1 to 30. Specific examplesthereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl,n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl,pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl,1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl,2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl,cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl,2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl,1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl,4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, a cycloalkyl group is not particularlylimited, but has preferably 3 to 30 carbon atoms, and specific examplesthereof include cyclopropyl, cyclobutyl, cyclopentyl,3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl,cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be straight-chained,branch-chained, or cyclic. The number of carbon atoms of the alkoxygroup is not particularly limited, but is preferably 1 to 30. Specificexamples thereof include methoxy, ethoxy, n-propoxy, isopropoxy,i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy,neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy,2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy,p-methylbenzyloxy, and the like, but are not limited thereto.

In the present specification, the amine group may be selected from thegroup consisting of —NH₂; an alkylamine group; an N-alkylarylaminegroup; an arylamine group; an N-arylheteroarylamine group; anN-alkylheteroarylamine group; and a heteroarylamine group, and thenumber of carbon atoms thereof is not particularly limited, but ispreferably 1 to 30. Specific examples of the amine group include amethylamine group, a dimethylamine group, an ethylamine group, adiethylamine group, a phenylamine group, a naphthylamine group, abiphenylamine group, an anthracenylamine group, a9-methyl-anthracenylamine group, a diphenylamine group, anN-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylaminegroup, a triphenylamine group, an N-phenylbiphenylamine group; anN-phenylnaphthylamine group; an N-biphenylnaphthylamine group; anN-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; anN-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; anN-phenyl terphenylamine group; an N-phenanthrenylfluorenylamine group;an N-biphenylfluorenylamine group, and the like, but are not limitedthereto.

In the present specification, the N-alkylarylamine group means an aminegroup in which an alkyl group and an aryl group are substituted with Nof the amine group. In the present specification, theN-arylheteroarylamine group means an amine group in which an aryl groupand a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group means anamine group in which an alkyl group and a heteroarylamine group aresubstituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group,the N-arylalkylamine group, the alkylthioxy group, the alkylsulfoxygroup, and the N-alkylheteroarylamine group is the same as theabove-described examples of the alkyl group. Specifically, examples ofthe alkylthioxy group include a methylthioxy group, an ethylthioxygroup, a tert-butylthioxy group, a hexylthioxy group, an octylthioxygroup, and the like, and examples of the alkylsulfoxy group includemesyl, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxygroup, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be straight-chainedor branch-chained, and the number of carbon atoms thereof is notparticularly limited, but is preferably 2 to 30. Specific examplesthereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl,1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl,2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl,2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group,and the like, but are not limited thereto.

In the present specification, specific examples of a silyl group includea trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilylgroup, a vinyldimethylsilyl group, a propyldimethylsilyl group, atriphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, andthe like, but are not limited thereto.

In the present specification, the boron group may be —BR₁₀₀R₁₀₁, andR₁₀₀ and R₁₀₁ are the same as or different from each other, and may beeach independently selected from the group consisting of hydrogen;deuterium; halogen; a nitrile group; a substituted or unsubstitutedmonocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; asubstituted or unsubstituted straight-chained or branch-chained alkylgroup having 1 to 30 carbon atoms; a substituted or unsubstitutedmonocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and asubstituted or unsubstituted monocyclic or polycyclic heteroaryl grouphaving 2 to 30 carbon atoms.

In the present specification, specific examples of the phosphine oxidegroup include a diphenylphosphine oxide group, dinaphthylphosphineoxide, and the like, but are not limited thereto.

In the present specification, an aryl group is not particularly limited,but has preferably 6 to 30 carbon atoms, and the aryl group may bemonocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbonatoms thereof is not particularly limited, but is preferably 6 to 30.Specific examples of the monocyclic aryl group include a phenyl group, abiphenyl group, a terphenyl group, and the like, but are not limitedthereto.

When the aryl group is a polycyclic aryl group, the number of carbonatoms thereof is not particularly limited, but is preferably 10 to 30.Specific examples of the polycyclic aryl group include a naphthyl group,an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenylgroup, a phenalenyl group, a perylenyl group, a chrysenyl group, afluorenyl group, and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted,and adjacent substituents may combine with each other to form a ring.

When the fluorenyl group is substituted, the fluorenyl group may be

and the like. However, the fluorenyl group is not limited thereto.

In the present specification, the “adjacent” group may mean asubstituent substituted with an atom directly linked to an atom in whichthe corresponding substituent is substituted, a substituent disposedsterically closest to the corresponding substituent, or anothersubstituent substituted with an atom in which the correspondingsubstituent is substituted. For example, two substituents substituted atthe ortho position in a benzene ring and two substituents substitutedwith the same carbon in an aliphatic ring may be interpreted as groupswhich are “adjacent” to each other.

In the present specification, the aryl group in the aryloxy group, thearylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, theN-arylheteroarylamine group, and the arylphosphine group is the same asthe above-described examples of the aryl group. Specifically, examplesof the aryloxy group include a phenoxy group, a p-tolyloxy group, anm-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxygroup, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxygroup, and the like, examples of the arylthioxy group include aphenylthioxy group, a 2-methylphenylthioxy group, a4-tert-butylphenylthioxy group, and the like, and examples of thearylsulfoxy group include a benzenesulfoxy group, a p-toluenesulfoxygroup, and the like, but the examples are not limited thereto.

In the present specification, examples of an arylamine group include asubstituted or unsubstituted monoarylamine group, a substituted orunsubstituted diarylamine group, or a substituted or unsubstitutedtriarylamine group. The aryl group in the arylamine group may be amonocyclic aryl group or a polycyclic aryl group. The arylamine groupincluding two or more aryl groups may include a monocyclic aryl group, apolycyclic aryl group, or both a monocyclic aryl group and a polycyclicaryl group. For example, the aryl group in the arylamine group may beselected from the above-described examples of the aryl group.

In the present specification, a heteroaryl group includes one or more ofan atom other than carbon, that is, a heteroatom, and specifically, theheteroatom may include one or more atoms selected from the groupconsisting of O, N, Se, and S, and the like. The number of carbon atomsthereof is not particularly limited, but is preferably 2 to 30, and theheteroaryl group may be monocyclic or polycyclic. Examples of theheterocyclic group include a thiophene group, a furanyl group, a pyrrolegroup, an imidazolyl group, a thiazolyl group, an oxazolyl group, anoxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidylgroup, a triazinyl group, a triazolyl group, an acridyl group, apyridazinyl group, a pyrazinyl group, a qinolinyl group, a quinazolinylgroup, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidylgroup, a pyridopyrazinyl group, a pyrazinopyrazinyl group, anisoquinolinyl group, an indolyl group, a carbazolyl group, abenzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, abenzocarbazolyl group, a benzothiophene group, a dibenzothiophene group,a benzofuranyl group, a phenanthrolinyl group (phenanthroline), athiazolyl group, an isoxazolyl group, an oxadiazolyl group, athiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, adibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, examples of a heteroarylamine groupinclude a substituted or unsubstituted monoheteroarylamine group, asubstituted or unsubstituted diheteroarylamine group, or a substitutedor unsubstituted triheteroarylamine group. The heteroarylamine groupincluding two or more heteroaryl groups may include a monocyclicheteroaryl group, a polycyclic heteroaryl group, or both a monocyclicheteroaryl group and a polycyclic heteroaryl group. For example, theheteroaryl group in the heteroarylamine group may be selected from theabove-described examples of the heteroaryl group.

In the present specification, examples of the heteroaryl group in theN-arylheteroarylamine group and the N-alkylheteroarylamine group are thesame as the above-described examples of the heteroaryl group.

In the present specification, the arylene group means that there are twobonding positions in an aryl group, that is, a divalent group. Theabove-described description on the aryl group may be applied, exceptthat the arylene groups are each a divalent group.

In the present specification, the heteroarylene group means that thereare two bonding positions in a heteroaryl group, that is, a divalentgroup. The above-described description on the heteroaryl group may beapplied, except that these are each a divalent group.

In the present specification, in a substituted or unsubstituted ringformed by combining adjacent groups, the “ring” means a substituted orunsubstituted hydrocarbon ring; or a substituted or unsubstituted heteroring.

In the present specification, a ring means a substituted orunsubstituted hydrocarbon ring; or a substituted or unsubstituted heteroring.

In the present specification, a hydrocarbon ring may be an aromaticring, an aliphatic ring, or a fused ring of the aromatic ring and thealiphatic ring, and may be selected from the examples of the cycloalkylgroup or the aryl group, except for the hydrocarbon ring which is notmonovalent.

In the present specification, an aromatic ring may be monocyclic orpolycyclic, and may be selected from the examples of the aryl group,except for the aromatic ring which is not monovalent.

In the present specification, a hetero ring includes one or more of anatom other than carbon, that is, a heteroatom, and specifically, theheteroatom may include one or more atoms selected from the groupconsisting of O, N, Se, and S, and the like. The hetero ring may bemonocyclic or polycyclic, may be an aromatic ring, an aliphatic ring, ora fused ring of the aromatic ring and the aliphatic ring, and may beselected from the examples of the heteroaryl group, except for thehetero ring which is not monovalent.

According to an exemplary embodiment of the present specification,Chemical Formula 1 is represented by any one of the following ChemicalFormulae 1-1 to 1-6.

In Chemical Formulae 1-1 to 1-6,

the definitions of X1 and R1 to R16 are the same as those in ChemicalFormula 1,

the definitions of L1, Ar1, and Ar2 are the same as those in ChemicalFormula B,

R101 to R103 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a nitrile group; a nitro group; ahydroxy group; a carbonyl group; an ester group; an imide group; anamide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted amine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group,

r101, r102, and r103 are each an integer of 1 to 3, and

when r101, r102, and r103 are each 2 or more, two or more structures inthe parenthesis are the same as or different from each other.

According to an exemplary embodiment of the present specification,Chemical Formula 1 is represented by any one of the following ChemicalFormulae 1-7 to 1-18.

In Chemical Formulae 1-7 to 1-18,

the definitions of R1 to R16 are the same as those in Chemical Formula1,

the definitions of L1, Ar1, and Ar2 are the same as those in ChemicalFormula B,

R101 to R103 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a nitrile group; a nitro group; ahydroxy group; a carbonyl group; an ester group; an imide group; anamide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted amine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group,

r101, r102, and r103 are each an integer of 1 to 3, and

when r101, r102, and r103 are each 2 or more, two or more structures inthe parenthesis are the same as or different from each other.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R13 to R16 are hydrogen.

According to an exemplary embodiment of the present specification, inChemical Formula 1, any one of R1 to R12 is Chemical Formula B, and theothers are hydrogen.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R1 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R2 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R3 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R4 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R5 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R6 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R7 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R8 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R9 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R10 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R11 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula 1, R12 is Chemical Formula B.

According to an exemplary embodiment of the present specification, inChemical Formula B, L1 is a direct bond; or a substituted orunsubstituted aryl group.

According to an exemplary embodiment of the present specification, inChemical Formula B, L1 is a direct bond; or an aryl group.

According to an exemplary embodiment of the present specification, inChemical Formula B, L1 is a direct bond; a substituted or unsubstitutedphenylene group; a substituted or unsubstituted biphenylylene group; ora substituted or unsubstituted naphthylene group.

According to an exemplary embodiment of the present specification, inChemical Formula B, L1 is a direct bond; a phenylene group; abiphenylylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, inChemical Formula B, An and Ar2 are the same as or different from eachother, and are each independently an aryl group which is unsubstitutedor substituted with one or more selected from the group consisting of anaryl group unsubstituted or substituted with an alkyl group, an alkylgroup, and an amine group; or a heteroaryl group which is unsubstitutedor substituted with an aryl group.

According to an exemplary embodiment of the present specification, inChemical Formula B, Ar1 and Ar2 are the same as or different from eachother, and are each independently a substituted or unsubstituted phenylgroup; a substituted or unsubstituted biphenyl group; a substituted orunsubstituted terphenyl group; a substituted or unsubstitutedquarterphenyl group; a substituted or unsubstituted naphthyl group; asubstituted or unsubstituted fluorenyl group; a substituted orunsubstituted spirobifluorenyl group; a substituted or unsubstitutedtriphenylenyl group; a substituted or unsubstituted phenanthrenylenegroup; a substituted or unsubstituted carbazolyl group; a substituted orunsubstituted dibenzofuranyl group; or a substituted or unsubstituteddibenzothiophene group.

According to an exemplary embodiment of the present specification, inChemical Formula B, Ar1 and Ar2 are the same as or different from eachother, and are each independently a phenyl group, which is unsubstitutedor substituted with an aryl group unsubstituted or substituted with analkyl group, or an amine group; a biphenyl group which is unsubstitutedor substituted with an aryl group; a terphenyl group which isunsubstituted or substituted with an aryl group; a quarterphenyl group;a naphthyl group; a fluorenyl group which is unsubstituted orsubstituted with one or more from the group consisting of an alkyl groupand an aryl group; a spirobifluorenyl group; a triphenylenyl group; aphenanthrenylene group; a carbazolyl group which is unsubstituted orsubstituted with an aryl group; a dibenzofuranyl group; or adibenzothiophene group.

According to an exemplary embodiment of the present specification, inChemical Formula B, Ar1 and Ar2 are the same as or different from eachother, and are each independently a phenyl group which is unsubstitutedor substituted with a phenyl group, a biphenyl group, a terphenyl group,a naphthyl group, a phenanthrenyl group, a fluorenyl group substitutedwith a methyl group, or a diphenylamine group; a biphenyl group which isunsubstituted or substituted with a phenyl group or a biphenyl group; aterphenyl group which is unsubstituted or substituted with a phenylgroup; a quarterphenyl group; a naphthyl group; a fluorenyl group whichis unsubstituted or substituted with one or more from the groupconsisting of a methyl group, a phenyl group, and a naphthyl group; aspirobifluorenyl group; a triphenylenyl group; a phenanthrenylene group;a carbazolyl group which is unsubstituted or substituted with a phenylgroup; a dibenzofuranyl group; or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, inChemical Formula B, Ar1 and Ar2 combine with each other to form asubstituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, inChemical Formula B, Ar1 and Ar2 combine with each other to form a ringrepresented by a structure of the following Chemical Formula C.

In Chemical Formula C,

X2 is CRR′, NR″, O, or S,

R, R′, R″, R201, and R202 are the same as or different from each other,and are each independently hydrogen; a substituted or unsubstitutedalkyl group; or a substituted or unsubstituted aryl group,

r201 and r202 are each an integer of 1 to 4,

when r201 and r202 are each 2 or more, two or more structures in theparenthesis are the same as or different from each other, and

is a moiety bonded to L1 of Chemical Formula B.

According to another exemplary embodiment of the present specification,in Chemical Formula C, R and R′ are the same as or different from eachother, and are each independently a substituted or unsubstituted alkylgroup.

According to still another exemplary embodiment of the presentspecification, in Chemical Formula C, R and R′ are the same as ordifferent from each other, and are each independently an alkyl group.

According to yet another exemplary embodiment of the presentspecification, in Chemical Formula C, R and R′ are a methyl group.

According to still yet another exemplary embodiment of the presentspecification, in Chemical Formula C, R and R″ are a substituted orunsubstituted aryl group.

According to a further exemplary embodiment of the presentspecification, in Chemical Formula C, R and R″ are an aryl group.

According to another further exemplary embodiment of the presentspecification, in Chemical Formula C, R″ is a phenyl group.

According to still another further exemplary embodiment of the presentspecification, in Chemical Formula C, R201 and R202 are the same as ordifferent from each other, and are each independently hydrogen; or asubstituted or unsubstituted aryl group.

According to yet another further exemplary embodiment of the presentspecification, in Chemical Formula C, R201 and R202 are the same as ordifferent from each other, and are each independently hydrogen; or anaryl group.

According to still yet another further exemplary embodiment of thepresent specification, in Chemical Formula C, R201 and R202 are the sameas or different from each other, and are each independently hydrogen; ora phenyl group.

According to still yet another exemplary embodiment of the presentspecification, Chemical Formula C is represented by any one of thefollowing structures.

According to an exemplary embodiment of the present specification,Chemical Formula 1 is selected from the following compounds.

An exemplary embodiment of the present specification provides an organiclight emitting device including: a first electrode; a second electrodeprovided to face the first electrode; and one or more organic materiallayers provided between the first electrode and the second electrode, inwhich one or more layers of the organic material layers include theabove-described spiro structure compound.

According to an exemplary embodiment of the present specification, theorganic material layer of the organic light emitting device of thepresent specification may also be composed of a single-layeredstructure, but may be composed of a multi-layered structure in which twoor more organic material layers are stacked. For example, the organiclight emitting device of the present invention may have a structureincluding a hole injection layer, a hole transport layer, an electronblocking layer, a light emitting layer, a hole blocking layer, anelectron transport layer, an electron injection layer, and the like asorganic material layers. However, the structure of the organic lightemitting device is not limited thereto, and may include fewer or moreorganic layers.

For example, the structure of the organic light emitting device of thepresent specification may have a structure as illustrated in FIGS. 1 and2, but is not limited thereto.

FIG. 1 exemplifies the structure of an organic light emitting device 10in which a first electrode 30, a light emitting layer 40, and a secondelectrode 50 are sequentially stacked on a substrate 20. FIG. 1 is anexemplified structure of the organic light emitting device according toan exemplary embodiment of the present specification, and may furtherinclude other organic material layers.

FIG. 2 exemplifies the structure of an organic light emitting device inwhich a first electrode 30, a hole injection layer 60, a hole transportlayer 70, a light emitting layer 40, an electron transport layer 80, anelectron injection layer 90, and a second electrode 50 are sequentiallystacked on a substrate 20. FIG. 2 is an exemplified structure accordingto exemplary embodiments of the present specification, and may furtherinclude other organic material layers.

According to an exemplary embodiment of the present specification, theorganic material layer includes a hole injection layer, and the holeinjection layer includes the spiro structure compound represented byChemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer includes a hole transport layer, and the holetransport layer includes the spiro structure compound represented byChemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer includes a hole control layer, and the holecontrol layer includes the spiro structure compound represented byChemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the spiro structure compound represented byChemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the spiro structure compound represented byChemical Formula 1 as a dopant of the light emitting layer.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes a compound represented by the following ChemicalFormula 1-A.

In Chemical Formula 1-A,

n1 is an integer of 1 or more,

Ar3 is a substituted or unsubstituted monovalent or more benzofluorenegroup; a substituted or unsubstituted monovalent or more fluoranthenegroup; a substituted or unsubstituted monovalent or more pyrene group;or a substituted or unsubstituted monovalent or more chrysene group,

L1 is a direct bond; a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group,

Ar4 and Ar5 are the same as or different from each other, and are eachindependently a substituted or unsubstituted aryl group; a substitutedor unsubstituted silyl group; a substituted or unsubstituted alkylgroup; a substituted or unsubstituted arylalkyl group; or a substitutedor unsubstituted heteroaryl group, or may combine with each other toform a substituted or unsubstituted ring, and

when n1 is 2 or more, two or more structures in the parenthesis are thesame as or different from each other.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the compound represented by Chemical Formula 1-Aas a dopant of the light emitting layer.

According to an exemplary embodiment of the present specification, L1 isa direct bond.

According to an exemplary embodiment of the present specification, n1 is2.

In an exemplary embodiment of the present specification, Ar3 is adivalent pyrene group which is unsubstituted or substituted withdeuterium, a methyl group, an ethyl group, an isopropyl group, or atert-butyl group; or a divalent chrysene group which is unsubstituted orsubstituted with deuterium, a methyl group, an ethyl group, or atert-butyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a substituted or unsubstituted aryl group having 6 to 30carbon atoms.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently an aryl group which is unsubstituted or substituted with asilyl group which is substituted with a methyl group, an ethyl group, anisopropyl group, a tert-butyl group, a nitrile group, or an alkyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently an aryl group which is unsubstituted or substituted withsilyl group which is substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently an aryl group which is unsubstituted or substituted with atrimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a substituted or unsubstituted phenyl group; a substitutedor unsubstituted biphenyl group; or a substituted or unsubstitutedterphenyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a phenyl group which is unsubstituted or substituted witha methyl group, an ethyl group, an isopropyl group, a tert-butyl group,a nitrile group, or a trimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a biphenyl group which is unsubstituted or substitutedwith a methyl group, an ethyl group, a tert-butyl group, a nitrilegroup, or a trimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a terphenyl group which is unsubstituted or substitutedwith a methyl group, an ethyl group, a tert-butyl group, a nitrilegroup, or a trimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a substituted or unsubstituted heteroaryl group having 6to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a heteroaryl group which is unsubstituted or substitutedwith a methyl group, an ethyl group, a tert-butyl group, a nitrilegroup, a silyl group substituted with an alkyl group, or a phenyl group.

According to an exemplary embodiment of the present specification, Ar4and Ar5 are the same as or different from each other, and are eachindependently a dibenzofuran group which is unsubstituted or substitutedwith a methyl group, an ethyl group, a tert-butyl group, a nitrilegroup, a trimethylsilyl group, or a phenyl group.

According to an exemplary embodiment of the present specification,Chemical Formula 1-A is selected from the following compounds.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes a compound represented by the following ChemicalFormula 2-A.

In Chemical Formula 2-A,

Ar11 and Ar12 are the same as or different from each other, and are eachindependently a substituted or unsubstituted monocyclic aryl group; or asubstituted or unsubstituted polycyclic aryl group, and

G1 to G8 are the same as or different from each other, and are eachindependently hydrogen; a substituted or unsubstituted monocyclic arylgroup; or a substituted or unsubstituted polycyclic aryl group.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the compound represented by Chemical Formula 2-Aas a host of the light emitting layer.

According to an exemplary embodiment of the present specification, Ar11and Ar12 are the same as or different from each other, and are eachindependently a substituted or unsubstituted polycyclic aryl group.

According to an exemplary embodiment of the present specification, Ar11and Ar12 are the same as or different from each other, and are eachindependently a substituted or unsubstituted polycyclic aryl grouphaving 10 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar11and Ar12 are the same as or different from each other, and are eachindependently a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, Ar11and Ar12 are the same as or different from each other, and are eachindependently a substituted or unsubstituted 1-naphthyl group.

According to an exemplary embodiment of the present specification, Ar11and Ar12 are a 1-naphthyl group.

According to an exemplary embodiment of the present specification, G1 toG8 are hydrogen.

According to an exemplary embodiment of the present specification,Chemical Formula 2-A is selected from the following compound.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the compound represented by Chemical Formula 1-Aas a dopant of the light emitting layer, and includes the compoundrepresented by Chemical Formula 2-A as a host of the light emittinglayer.

According to an exemplary embodiment of the present specification, theorganic material layer may further include one or more layers selectedfrom the group consisting of a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, and anelectron injection layer.

The organic light emitting device of the present specification may bemanufactured by the materials and methods known in the art, except thatone or more layers of the organic material layers include the spirostructure compound of the present specification, that is, the spirostructure compound represented by Chemical Formula 1.

When the organic light emitting device includes a plurality of organicmaterial layers, the organic material layers may be formed of the samematerial or different materials.

For example, the organic light emitting device of the presentspecification may be manufactured by sequentially stacking a firstelectrode, an organic material layer, and a second electrode on asubstrate. In this case, the organic light emitting device may bemanufactured by depositing a metal or a metal oxide having conductivity,or an alloy thereof on a substrate to form a first electrode, forming anorganic material layer including a hole injection layer, a holetransport layer, a light emitting layer, and an electron transport layerthereon, and then depositing a material, which may be used as a secondelectrode, thereon, by using a physical vapor deposition (PVD) methodsuch as sputtering or e-beam evaporation. In addition to the methoddescribed above, an organic light emitting device may be made bysequentially depositing a second electrode material, an organic materiallayer, and a first electrode material on a substrate. Further, the spirostructure compound represented by Chemical Formula 1 may be formed as anorganic material layer by not only a vacuum deposition method, but alsoa solution application method when an organic light emitting device ismanufactured. Here, the solution application method means spin coating,dip coating, doctor blading, inkjet printing, screen printing, a spraymethod, roll coating, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, thefirst electrode is a positive electrode, and the second electrode is anegative electrode.

According to another exemplary embodiment of the present specification,the first electrode is a negative electrode, and the second electrode isa positive electrode.

As the positive electrode material, a material having a large workfunction is usually preferred so as to smoothly inject holes into anorganic material layer. Specific examples of the positive electrodematerial which may be used in the present invention include: a metal,such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; ametal oxide, such as zinc oxide, indium oxide, indium tin oxide (ITO),and indium zinc oxide (IZO); a combination of metal and oxide, such asZnO:Al or SnO₂:Sb; an electrically conductive polymer, such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT),polypyrrole, and polyaniline, and the like, but are not limited thereto.

As the negative electrode material, a material having a small workfunction is usually preferred so as to smoothly inject electrons into anorganic material layer. Specific examples of the negative electrodematerial include: a metal, such as magnesium, calcium, sodium,potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum,silver, tin, and lead, or alloys thereof; a multi-layered structuralmaterial, such as LiF/Al or LiO₂/Al and Mg/Ag, and the like, but are notlimited thereto.

The hole injection layer is a layer which injects holes from anelectrode, and a hole injection material is preferably a compound whichhas a capability of transporting holes and thus has an effect ofinjecting holes at a positive electrode and an excellent effect ofinjecting holes for a light emitting layer or a light emitting material,prevents excitons produced from the light emitting layer from moving toan electron injection layer or an electron injection material, and isalso excellent in the ability to form a thin film. It is preferred thatthe highest occupied molecular orbital (HOMO) of the hole injectionmaterial is between the work function of the positive electrode materialand the HOMO of a peripheral organic material layer. Specific examplesof the hole injection material include metal porphyrin, oligothiophene,an arylamine-based organic material, a hexanitrilehexaazatriphenylene-based organic material, a quinacridone-based organicmaterial, a perylene-based organic material, anthraquinone, apolyaniline and polythiophene-based electrically conductive polymer, andthe like, but are not limited thereto.

The hole transport layer is a layer which receives holes from a holeinjection layer and transports the holes to a light emitting layer, anda hole transport material is suitably a material which may receive holesfrom a positive electrode or a hole injection layer to transfer theholes to a light emitting layer, and has a large mobility for the holes.Specific examples thereof include an arylamine-based organic material,an electrically conductive polymer, a block copolymer in which aconjugate portion and a non-conjugate portion are present together, andthe like, but are not limited thereto.

The hole control layer serves to effectively receive holes transferredfrom a hole transport layer and adjust the hole mobility, and thusserves to adjust the amount of holes transferred to a light emittinglayer. Further, the hole control layer may simultaneously serve as anelectron barrier, which allows electrons supplied from the lightemitting layer not to be transferred to the hole transport layer. Thismay increase the light emitting efficiency by maximizing the balancebetween holes and electrons in the light emitting layer, the lifetime ofthe device may be improved through the electron stability of the holecontrol layer, and materials known in the art may be used.

A light emitting material for the light emitting layer is a materialwhich may receive holes and electrons from a hole transport layer and anelectron transport layer, respectively, and combine the holes and theelectrons to emit light in a visible ray region, and is preferably amaterial having good quantum efficiency to fluorescence orphosphorescence. Specific examples thereof include: an8-hydroxy-quinoline aluminum complex (Alq₃); a carbazole-based compound;a dimerized styryl compound; BAlq; a 10-hydroxybenzoquinoline-metalcompound; a benzoxazole, benzothiazole and benzimidazole-based compound;a poly(p-phenylenevinylene) (PPV)-based polymer; a Spiro compound;polyfluorene, lubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopantmaterial. Examples of the host material include a fused aromatic ringderivative, or a hetero ring-containing compound, and the like.Specifically, examples of the fused aromatic ring derivative include ananthracene derivative, a pyrene derivative, a naphthalene derivative, apentacene derivative, a phenanthrene compound, a fluoranthene compound,and the like, and examples of the hetero ring-containing compoundinclude a carbazole derivative, a dibenzofuran derivative, a ladder-typefuran compound, a pyrimidine derivative, and the like, but the examplesthereof are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, astyrylamine compound, a boron complex, a fluoranthene compound, a metalcomplex, and the like. Specifically, the aromatic amine derivative is afused aromatic ring derivative having a substituted or unsubstitutedarylamino group, and examples thereof include a pyrene, an anthracene, achrysene, a periflanthene, and the like, which have an arylamino group,and the styrylamine compound is a compound in which a substituted orunsubstituted arylamine is substituted with at least one arylvinylgroup, and one or two or more substituents selected from the groupconsisting of an aryl group, a silyl group, an alkyl group, a cycloalkylgroup, and an arylamino group are substituted or unsubstituted. Specificexamples thereof include styrylamine, styryldiamine, styryltriamine,styryltetramine, and the like, but are not limited thereto. Further,examples of the metal complex include an iridium complex, a platinumcomplex, and the like, but are not limited thereto.

The electron transport layer is a layer which receives electrons from anelectron injection layer and transports the electrons to a lightemitting layer, and an electron transport material is suitably amaterial which may receive electrons well from a negative electrode andtransfer the electrons to a light emitting layer and has large mobilityfor the electrons. Specific examples thereof include: an Al complex of8-hydroxyquinoline; a complex including Alq₃; an organic radicalcompound; a hydroxyflavone-metal complex, and the like, but are notlimited thereto. The electron transport layer may be used with anydesired cathode material, as used according to the related art. Inparticular, appropriate examples of the cathode material are a typicalmaterial which has a low work function, followed by an aluminum layer ora silver layer. Specific examples thereof include cesium, barium,calcium, ytterbium, and samarium, in each case followed by an aluminumlayer or a silver layer.

The electron injection layer is a layer which injects electrons from anelectrode, and is preferably a compound which has a capability oftransporting electrons, has an effect of injecting electrons from anegative electrode and an excellent effect of injecting electrons into alight emitting layer or a light emitting material, prevents excitonsproduced from the light emitting layer from moving to a hole injectionlayer, and is also excellent in the ability to form a thin film.Specific examples thereof include fluorenone, anthraquinodimethane,diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole,imidazole, perylenetetracarboxylic acid, fluorenylidene methane,anthrone, and the like, and derivatives thereof, a metal complexcompound, a nitrogen-containing 5-membered ring derivative, and thelike, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum,tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc,bis(2-methyl-8-quinolinato) chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato) gallium,bis(2-methyl-8-quinolinato)(1-naphtholato) aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato) gallium, and the like, butare not limited thereto.

The organic light emitting device according to the present specificationmay be a top emission type, a bottom emission type, or a dual emissiontype according to the material to be used.

According to an exemplary embodiment of the present specification, thespiro structure compound represented by Chemical Formula 1 may beincluded in an organic solar cell or an organic transistor in additionto the organic light emitting device.

Hereinafter, the present specification will be described in detail withreference to Examples in order to specifically explain the presentspecification. However, the Examples according to the presentspecification may be modified in various forms, and it is notinterpreted that the scope of the present specification is limited tothe Examples described below in detail. The Examples of the presentspecification are provided to more completely explain the presentspecification to a person with ordinary skill in the art.

PREPARATION EXAMPLES

Preparation Example A-1 Preparation of Compound A-1

After benzofuran-2-boronic acid (30 g, 185 mmol) and1-bromo-2-iodobenzene (53.2 g, 189 mmol) were added to dioxane (300 ml),a 2M aqueous potassium carbonate solution (100 ml) was added thereto,tetrakistriphenyl-phosphinopalladium (4.28 g, 2 mol %) was putthereinto, and then the resulting mixture was heated and stirred for 4hours. The temperature was lowered to normal temperature, the reactionwas terminated, and then the potassium carbonate solution was removed toseparate the layers. After the solvent was removed, the residue wascolumned with hexane to prepare Compound A-1, which is a colorless oil(42.7 g, 85%).

MS[M+H]⁺=272.98

Preparation Example A-2 Preparation of Compound A-2

Compound A-2 was prepared by performing the synthesis in the same manneras in Preparation Example A-1, except that benzofuran-3-boronic acid wasused instead of benzofuran-2-boronic acid.

MS[M+H]⁺=272.98

Preparation Example A-3 Preparation of Compound A-3

Compound A-3 was prepared by performing the synthesis in the same manneras in Preparation Example A-2, except that1-bromo-3-chloro-2-iodobenzene was used instead of1-bromo-2-iodobenzene.

MS[M+H]⁺=306.94

Preparation Example A-4 Preparation of Compound A-4

Compound A-4 was prepared by performing the synthesis in the same manneras in Preparation Example A-1, except that benzothiophene-2-boronic acidwas used instead of benzofuran-2-boronic acid.

MS[M+H]+=288.96

Preparation Example A-5 Preparation of Compound A-5

Compound A-5 was prepared by performing the synthesis in the same manneras in Preparation Example A-1, except that benzothiophene-3-boronic acidwas used instead of benzofuran-2-boronic acid.

MS[M+H]⁺=288.96

Preparation Example B-1 Preparation of Compound B-1

After Compound A-1 (30 g, 110 mmol) was dissolved in THF (250 ml), thetemperature was lowered to −78° C., and then 2.5 M n-BuLi (57 ml) wasadded dropwise thereto, and after 30 minutes, 2-bromo-9H-fluoren-9-one(28.3 g, 109 mmol) was put thereinto, the temperature was increased toRT, and then the resulting mixture was stirred for 1 hour. After 1 N HClwas put thereinto and the resulting mixture was stirred for 30 minutes,the layers were separated to remove the solvent, and then the residuewas recrystallized with hexane to prepare Compound B-1 (47.2 g, 95%).

MS[M+H]⁺=453.04

Preparation Example B-2 Preparation of Compound B-2

Compound B-2 was prepared by performing the synthesis in the same manneras in Preparation Example B-1, except that 4-bromo-9H-fluoren-9-one wasused instead of 2-bromo-9H-fluoren-9-one.

MS[M+H]⁺=453.04

Preparation Example B-3 Preparation of Compound B-3

Compound B-3 was prepared by performing the synthesis in the same manneras in Preparation Example B-1, except that Compound A-2 was used insteadof Compound A-1.

MS[M+H]⁺=453.04

Preparation Example B-4 Preparation of Compound B-4

Compound B-4 was prepared by performing the synthesis in the same manneras in the synthesis of Preparation Example B-3, except that4-bromo-9H-fluoren-9-one was used instead of 2-bromo-9H-fluoren-9-one.

MS[M+H]⁺=453.04

Preparation Example B-5 Preparation of Compound B-5

Compound B-5 was prepared by performing the synthesis in the same manneras in Preparation Example B-1, except that Compound A-3 was used insteadof Compound A-1.

MS[M+H]⁺=453.04

Preparation Example B-6 Preparation of Compound B-6

Compound B-6 was prepared by performing the synthesis in the same manneras in Preparation Example B-1, except that Compound A-4 was used insteadof Compound A-1.

MS[M+H]⁺=469.02

Preparation Example B-7 Preparation of Compound B-7

Compound B-7 was prepared by performing the synthesis in the same manneras in Preparation Example B-6, except that 4-bromo-9H-fluoren-9-one wasused instead of 2-bromo-9H-fluoren-9-one.

MS[M+H]⁺=469.02

Preparation Example B-8 Preparation of Compound B-8

Compound B-8 was prepared by performing the synthesis in the same manneras in Preparation Example B-1, except that Compound A-5 was used insteadof Compound A-1.

MS[M+H]⁺=469.02

Preparation Example B-9 Preparation of Compound B-9

Compound B-9 was prepared by performing the synthesis in the same manneras in Preparation Example B-8, except that 4-bromo-9H-fluoren-9-one wasused instead of 2-bromo-9H-fluoren-9-one.

MS[M+H]+=469.02

Preparation Example B-10 Preparation of Compound B-10

Compound B-10 was prepared by performing the synthesis in the samemanner as in Preparation Example B-8, except that1-bromo-9H-fluoren-9-one was used instead of 2-bromo-9H-fluoren-9-one.

MS[M+H]+=469.02

Preparation Example C-1 Preparation of Compound C-1

After Compound B-1 (30 g, 66.4 mmol) was put into acetic acid (250 ml),10 ml of trifluoroacetic acid was added dropwise thereto, and theresulting mixture was stirred and refluxed. The temperature was loweredto normal temperature, the resulting product was neutralized with water,and then the filtered solid was recrystallized with ethyl acetate toprepare Compound C-1 (20 g, 70%).

MS[M+H]⁺=435.03

Preparation Example C-2 Preparation of Compound C-2

Compound C-2 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-2 was used insteadof Compound B-1.

MS[M+H]⁺=435.03

Preparation Example C-3 Preparation of Compound C-3

Compound C-3 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-3 was used insteadof Compound B-1.

MS[M+H]⁺=435.03

Preparation Example C-4 Preparation of Compound C-4

Compound C-4 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-4 was used insteadof Compound B-1.

MS[M+H]⁺=435.03

Preparation Example C-5 Preparation of Compound C-5

Compound C-5 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-5 was used insteadof Compound B-1.

MS[M+H]⁺=391.08

Preparation Example C-6 Preparation of Compound C-6

Compound C-6 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-6 was used insteadof Compound B-1.

MS[M+H]⁺=451.01

Preparation Example C-7 Preparation of Compound C-7

Compound C-7 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-7 was used insteadof Compound B-1.

MS[M+H]⁺=451.01

Preparation Example C-8 Preparation of Compound C-8

Compound C-8 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-8 was used insteadof Compound B-1.

MS[M+H]⁺=451.01

Preparation Example C-9 Preparation of Compound C-9

Compound C-9 was prepared by performing the synthesis in the same manneras in Preparation Example C-1, except that Compound B-9 was used insteadof Compound B-1.

MS[M+H]⁺=451.01

Preparation Example C-10 Preparation of Compound C-10

Compound C-10 was prepared by performing the synthesis in the samemanner as in Preparation Example C-1, except that Compound B-10 was usedinstead of Compound B-1.

MS[M+H]⁺=451.01

Preparation Example D-1 Preparation of Compound D-1

After Compound C-3 (20 g, 46 mmol) and 4-chlorophenylboronic acid (7.33g, 47 mmol) were added to tetrahydrofuran (300 ml), a 2M aqueouspotassium carbonate solution (100 ml) was added thereto,tetrakistriphenyl-phosphinopalladium (1.06 g, 0.92 mmol) was putthereinto, and then the resulting mixture was heated and stirred for 7hours. The temperature was lowered to normal temperature, the reactionwas terminated, and then the potassium carbonate solution was removed toseparate the layers. After the solvent was removed, the residue wasrecrystallized with tetrahydrofuran and ethyl acetate to prepareCompound D-1 (18.2 g, yield 25%).

MS[M+H]⁺=467.11

Preparation Example D-2 Preparation of Compound D-2

Compound D-2 was prepared by performing the synthesis in the same manneras in Preparation Example D-1, except that Compound C-9 was used insteadof Compound C-3.

MS[M+H]⁺=483.09

Preparation Example 1 Preparation of Compound 1

Compound C-1 (20 g, 46 mmol),4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline (16.9 g, 47 mmol), andsodium-t-butoxide (6.2 g, 64.4 mmol) were put into toluene and heatedand stirred and then the resulting mixture was refluxed, and[bis(tri-t-butylphosphine)]palladium (1.03 mg, 2 mmol %) was putthereinto. The temperature was lowered to normal temperature, thereaction was terminated, and then the resulting product wasrecrystallized by using tetrahydrofuran and ethyl acetate to prepareCompound 1 (28.3 g, 65%).

MS[M+H]⁺=716.29

Preparation Example 2 Preparation of Compound 2

Compound 2 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-2 was used insteadof Compound C-1, and N-phenyl-[1,1′:4′,1″-terphenyl]amine was usedinstead of 4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=676.26

Preparation Example 3 Preparation of Compound 3

Compound 3 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-3 was used insteadof Compound C-1, and N-(1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine wasused instead of 4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=676.26

Preparation Example 4 Preparation of Compound 4

Compound 4 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-3 was used insteadof Compound C-1, andN-(1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine was used insteadof 4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=716.29

Preparation Example 5 Preparation of Compound 5

Compound 5 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound D-1 was used insteadof Compound C-1, and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine was usedinstead of 4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=716.29

Preparation Example 6 Preparation of Compound 6

Compound 6 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-5 was used insteadof Compound C-1, and di([1,1′-biphenyl)-4-yl)amine was used instead of4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=676.26

Preparation Example 7 Preparation of Compound 7

Compound 7 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-6 was used insteadof Compound C-1, and di([1,1′-biphenyl)-4-yl)amine was used instead of4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=692.23

Preparation Example 8 Preparation of Compound 8

Compound 8 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-7 was used insteadof Compound C-1, and N-phenyl-[1,1′:4′,1″-terphenyl]amine was usedinstead of 4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=692.23

Preparation Example 9 Preparation of Compound 9

Compound 9 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound D-2 was used insteadof Compound C-1, andN-(1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine was used.

MS[M+H]⁺=808.30

Preparation Example 10 Preparation of Compound 10

Compound 10 was prepared by performing the synthesis in the same manneras in Preparation Example 1, except that Compound C-10 was used insteadof Compound C-1, and N,9-diphenyl-9H-carbazol-3-amine was used insteadof 4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline.

MS[M+H]⁺=705.30

Example 1-1

A glass substrate (Corning 7059 glass) thinly coated with indium tinoxide (ITO) to have a thickness of 1,000 Å was put into distilled waterin which a dispersant was dissolved, and ultrasonically washed. Aproduct manufactured by Fischer Co., was used as the detergent, anddistilled water twice filtered using a filter manufactured by MilliporeCo., was used as the distilled water. After the ITO was washed for 30minutes, ultrasonic washing was conducted twice repeatedly usingdistilled water for 10 minutes. After the washing using distilled waterwas completed, ultrasonic washing was conducted using isopropyl alcohol,acetone, and methanol solvents in this order, and drying was thenconducted.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited to have athickness of 500 Å on a transparent ITO electrode thus prepared, therebyforming a hole injection layer. Compound 1 (900 Å) synthesized inPreparation Example 1, which is a material for transporting holes, wasvacuum deposited thereon, and then HT2 was sequentially vacuum depositedto have a film thickness of 100 Å on the hole transport layer, therebyforming a hole control layer. As a light emitting layer, a compound ofhost H1 and dopant D1 (25:1) was vacuum deposited to have a thickness of300 Å. And then, the E1 compound (300 Å) was thermally vacuum depositedas an electron injection and transport layer. A negative electrode wasformed by sequentially depositing lithium fluoride (LiF) and aluminum tohave a thickness of 12 Å and 2,000 Å, respectively, on the electroninjection and transport layer, thereby manufacturing an organic lightemitting device.

In the aforementioned procedure, the deposition rates of the organicmaterial, lithium fluoride, and aluminum were maintained at 1 Å/sec, 0.2Å/sec, and 3 to 7 Å/sec, respectively.

Example 1-2

An experiment was performed in the same manner as in Example 1-1, exceptthat as the hole transport layer, Compound 3 was used instead ofCompound 1.

Example 1-3

An experiment was performed in the same manner as in ExperimentalExample 1-1, except that as the hole transport layer, Compound 4 wasused instead of Compound 1.

Example 1-4

An experiment was performed in the same manner as in ExperimentalExample 1-1, except that as the hole transport layer, Compound 5 wasused instead of Compound 1.

Example 1-5

An experiment was performed in the same manner as in ExperimentalExample 1-1, except that as the hole transport layer, Compound 7 wasused instead of Compound 1.

Example 1-6

An experiment was performed in the same manner as in ExperimentalExample 1-1, except that as the hole transport layer, Compound 10 wasused instead of Compound 1.

Comparative Example 1-1

An experiment was performed in the same manner as in ExperimentalExample 1-1, except that as the hole transport layer, the following HT1was used instead of Compound 1.

The device evaluation results of the organic light emitting devices inExamples 1-1 to 1-6 and Comparative Example 1-1 are shown in thefollowing Table 1.

TABLE 1 Current Hole transport Voltage efficiency 50 mA/cm² layermaterial (V) (cd/A) Comparative HT1 4.11 5.32 Example 1-1 Example 1-1Compound 1 3.70 5.61 Example 1-2 Compound 3 3.46 5.75 Example 1-3Compound 4 3.59 5.88 Example 1-4 Compound 5 3.66 5.91 Example 1-5Compound 7 3.71 5.55 Example 1-6 Compound 10 3.55 5.89

As in Table 1, it can be seen that the organic light emitting devices inExamples 1-1 to 1-6 manufactured by using the spiro structure compoundaccording to an exemplary embodiment of the present specificationexhibit low voltage and high efficiency characteristics as compared toComparative Example 1-1, which is a benzidine-type material.

Example 2-1

A glass substrate (Corning 7059 glass) thinly coated with indium tinoxide (ITO) to have a thickness of 1,000 Å was put into distilled waterin which a dispersant was dissolved, and ultrasonically washed. Aproduct manufactured by Fischer Co., was used as the detergent, anddistilled water twice filtered using a filter manufactured by MilliporeCo., was used as the distilled water. After the ITO was washed for 30minutes, ultrasonic washing was conducted twice repeatedly usingdistilled water for 10 minutes. After the washing using distilled waterwas completed, ultrasonic washing was conducted using isopropyl alcohol,acetone, and methanol solvents in this order, and drying was thenconducted.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited to have athickness of 500 Å on a transparent ITO electrode thus prepared, therebyforming a hole injection layer. HT1 (900 Å), which is a material fortransporting holes, was vacuum deposited thereon, and then Compound 2was vacuum deposited to have a film thickness of 100 Å on the holetransport layer, thereby forming a hole control layer. As a lightemitting layer, host H1 and dopant D1 (25:1) were vacuum deposited tohave a thickness of 300 Å. And then, E1 (300 Å) was thermally vacuumdeposited as an electron injection and transport layer. A negativeelectrode was formed by sequentially depositing lithium fluoride (LiF)and aluminum to have a thickness of 12 Å and 2,000 Å, respectively, onthe electron injection and transport layer, thereby manufacturing anorganic light emitting device.

In the aforementioned procedure, the deposition rates of the organicmaterial, lithium fluoride, and aluminum were maintained at 1 Å/sec, 0.2Å/sec, and 3 to 7 Å/sec, respectively.

Example 2-2

An experiment was performed in the same manner as in Example 2-1, exceptthat as the hole control layer, Compound 6 was used instead of Compound2.

Example 2-3

An experiment was performed in the same manner as in Example 2-1, exceptthat as the hole control layer, Compound 8 was used instead of Compound2.

Example 2-4

An experiment was performed in the same manner as in Example 2-1, exceptthat as the hole control layer, Compound 9 was used instead of Compound2.

Comparative Example 2-1

An experiment was performed in the same manner as in Example 2-1, exceptthat as the hole control layer, HT2 was used instead of Compound 2.

The device evaluation results of the organic light emitting devices inExamples 2-1 to 2-4 and Comparative Example 2-1 are shown in thefollowing Table 2.

TABLE 2 Experimental Example Hole control Voltage Current 50 mA/cm²layer material (V) efficiency (cd/A) Comparative HT2 4.02 5.11 Example2-1 Example 2-1 Compound 2 4.03 5.30 Example 2-2 Compound 6 3.56 5.76Example 2-3 Compound 8 4.01 5.02 Example 2-4 Compound 9 3.61 5.98

As in Table 2, it can be seen that the organic light emitting devices inExamples 2-1 to 2-4 manufactured by using the spiro structure compoundrepresented by Chemical Formula 1 according to an exemplary embodimentof the present specification exhibit low voltage and high efficiencycharacteristics as compared to the organic light emitting device inComparative Example 2-1, which uses HT2 which is a carbazole-typematerial.

In particular, when an oxygen group element is formed as in Compounds 6and 9 in the molecular structure of the spiro structure compoundrepresented by Chemical Formula 1 according to an exemplary embodimentof the present specification, there is an effect in that the performanceof the device is enhanced because Compounds 6 and 9 have high tripletenergy when used as a hole control layer.

The spiro structure compound represented by Chemical Formula 1 accordingto an exemplary embodiment of the present specification may serve totransport holes and adjust holes in an organic electronic deviceincluding an organic light emitting device, and the organic lightemitting device according to the present specification exhibitsexcellent characteristics in terms of efficiency, driving voltage, andstability.

EXPLANATION OF REFERENCE NUMERALS AND SYMBOLS

10, 11: Organic light emitting device

20: Substrate

30: First electrode

40: Light emitting layer

50: Second electrode

60: Hole injection layer

70: Hole transport layer

80: Electron transport layer

90: Electron injection layer

The invention claimed is:
 1. A Spiro structure compound represented bythe following Chemical Formula 1:

in Chemical Formula 1, X1 is O or S, and any one of R1 to R12 is thefollowing Chemical Formula B, and the others and R13 to R16 are the sameas or different from each other, and are each independently hydrogen;deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonylgroup; an ester group; an imide group; an amide group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedboron group; a substituted or unsubstituted amine group; a substitutedor unsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group,

in Chemical Formula B, L1 is a direct bond; a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group, and Ar1 and Ar2 are the same as or different fromeach other, and are each independently a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heteroaryl group, orcombine with each other to form a substituted or unsubstituted ring, andwhen R2 or R7 is Chemical Formula B and Ar1 and Ar2 each independently asubstituted or unsubstituted aryl group, at least one of Ar1 and Ar2 isa substituted or unsubstituted polycyclic aryl group, and the polycyclicaryl group is selected from a naphthyl group, an anthracenyl group, aphenanthrenyl group, a triphenylenyl group, a pyrenyl group, aphenalenyl group, a perylenyl group, a chrysenyl group, or a fluorenylgroup.
 2. The spiro structure compound of claim 1, wherein ChemicalFormula 1 is represented by any one of the following Chemical Formulae1-1 to 1-6:

in Chemical Formulae 1-1 to 1-6, the definitions of X1 and R1 to R16 arethe same as those in Chemical Formula 1, the definitions of L1, Ar1, andAr2 are the same as those in Chemical Formula B, R101 to R103 are thesame as or different from each other, and are each independentlyhydrogen; deuterium; a nitrile group; a nitro group; a hydroxy group; acarbonyl group; an ester group; an imide group; an amide group; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedcycloalkyl group; a substituted or unsubstituted alkoxy group; asubstituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted amine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group, r101, r102, and r103 are each an integerof 1 to 3, and when r101, r102, and r103 are each 2 or more, two or morestructures in the parenthesis are the same as or different from eachother.
 3. The Spiro structure compound of claim 1, wherein ChemicalFormula 1 is represented by any one of the following Chemical Formulae1-7 to 1-18:

in Chemical Formulae 1-7 to 1-18, the definitions of R1 to R16 are thesame as those in Chemical Formula 1, the definitions of L1, Ar1, and Artare the same as those in Chemical Formula B, R101 to R103 are the sameas or different from each other, and are each independently hydrogen;deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonylgroup; an ester group; an imide group; an amide group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedboron group; a substituted or unsubstituted amine group; a substitutedor unsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group, r101, r102, and r103 areeach an integer of 1 to 3, and when r101, r102, and r103 are each 2 ormore, two or more structures in the parenthesis are the same as ordifferent from each other.
 4. The spiro structure compound of claim 1,wherein L1 is a direct bond; a substituted or unsubstituted phenylenegroup; a substituted or unsubstituted biphenylylene group; or asubstituted or unsubstituted naphthylene group.
 5. The spiro structurecompound of claim 1, wherein Ar1 and Ar2 are the same as or differentfrom each other, and are each independently a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted terphenyl group; a substituted orunsubstituted quarterphenyl group; a substituted or unsubstitutednaphthyl group; a substituted or unsubstituted anthracenyl group; asubstituted or unsubstituted pyrenyl group; a substituted orunsubstituted perylenyl group; a substituted or unsubstituted chrysenylgroup; a substituted or unsubstituted fluorenyl group; a substituted orunsubstituted spirobifluorenyl group; a substituted or unsubstitutedtriphenylenyl group; a substituted or unsubstituted phenanthrenyl group;a substituted or unsubstituted carbazolyl group; a substituted orunsubstituted dibenzofuranyl group; or a substituted or unsubstituteddibenzothiophene group.
 6. The spiro structure compound of claim 1,wherein Ar1 and Ar2 combine with each other to be represented by astructure of the following Chemical Formula C:

in Chemical Formula C, X2 is CRR′, NR″, O, or S, R, R′, R″, R201, andR202 are the same as or different from each other, and are eachindependently hydrogen; a substituted or unsubstituted alkyl group; or asubstituted or unsubstituted aryl group, r201 and r202 are each aninteger of 1 to 4, when r201 and r202 are each 2 or more, two or morestructures in the parenthesis are the same as or different from eachother, and

is a moiety bonded to L1 of Chemical Formula B.
 7. The spiro structurecompound of claim 1, wherein Chemical Formula 1 is selected from thefollowing compounds:


8. An organic light emitting device comprising: a first electrode; asecond electrode provided to face the first electrode; and one or moreorganic material layers provided between the first electrode and thesecond electrode, wherein the one or more organic material layerscomprise the spiro structure compound of claim
 1. 9. The organic lightemitting device of claim 8, wherein the one or more organic materiallayers comprise a hole injection layer, and the hole injection layercomprises the spiro structure compound.
 10. The organic light emittingdevice of claim 8, wherein the one or more organic material layerscomprise a hole transport layer, and the hole transport layer comprisesthe spiro structure compound.
 11. The organic light emitting device ofclaim 8, wherein the one or more organic material layers comprise a holecontrol layer, and the hole control layer comprises the spiro structurecompound.
 12. The organic light emitting device of claim 8, wherein theone or more organic material layers comprise a light emitting layer, andthe light emitting layer comprises the spiro structure compound.
 13. Theorganic light emitting device of claim 8, wherein the one or moreorganic material layers comprise a light emitting layer, and the lightemitting layer comprises the spiro structure compound as a dopant of thelight emitting layer.
 14. An organic light emitting device comprising: afirst electrode; a second electrode provided to face the firstelectrode; and one or more organic material layers provided between thefirst electrode and the second electrode, wherein the one or moreorganic material layers comprises a sprio structure compound ofrepresented by the following Chemical Formula 1:

in Chemical Formula 1, X1 is O or S, and any one of R1 to R12 is thefollowing Chemical Formula B, and the others and R13 to R16 are the sameas or different from each other, and are each independently hydrogen;deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonylgroup; an ester group; an imide group; an amide group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedboron group; a substituted or unsubstituted amine group; a substitutedor unsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group,

in Chemical Formula B, L1 is a direct bond; a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group, and Ar1 and Ar2 are the same as or different fromeach other, and are each independently a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heteroaryl group, orcombine with each other to form a substituted or unsubstituted ring,wherein the one or more organic material layers comprise a lightemitting layer, and the light emitting layer comprises a compoundrepresented by the following Chemical Formula 1-A:

in Chemical Formula 1-A, n1 is an integer of 1 or more, Ar3 is asubstituted or unsubstituted monovalent or more benzofluorene group; asubstituted or unsubstituted monovalent or more fluoranthene group; asubstituted or unsubstituted monovalent or more pyrene group; or asubstituted or unsubstituted monovalent or more chrysene group, L1 is adirect bond; a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group, Ar4 and Ar5 are thesame as or different from each other, and are each independently asubstituted or unsubstituted aryl group; a substituted or unsubstitutedsilyl group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted arylalkyl group; or a substituted or unsubstitutedheteroaryl group, or optionally combine with each other to form asubstituted or unsubstituted ring, and when n1 is 2 or more, two or morestructures in the parenthesis are the same as or different from eachother.
 15. The organic light emitting device of claim 14, wherein L1 isa direct bond, Ar3 is a divalent pyrene group, Ar4 and Ar5 are the sameas or different from each other, and are each independently an arylgroup which is unsubstituted or substituted with a silyl group which issubstituted with an alkyl group, and n1 is
 2. 16. The organic lightemitting device of claim 8, wherein the one or more organic materiallayers comprises a light emitting layer, and the light emitting layercomprises a compound represented by the following Chemical Formula 2-A:

in Chemical Formula 2-A, Ar11 and Ar12 are the same as or different fromeach other, and are each independently a substituted or unsubstitutedmonocyclic aryl group; or a substituted or unsubstituted polycyclic arylgroup, and G1 to G8 are the same as or different from each other, andare each independently hydrogen; a substituted or unsubstitutedmonocyclic aryl group; or a substituted or unsubstituted polycyclic arylgroup.
 17. The organic light emitting device of claim 16, wherein Ar11and Ar12 are a 1-naphthyl group, and G1 to G8 are hydrogen.
 18. Theorganic light emitting device of claim 14, wherein the light emittinglayer comprises a compound represented by the following Chemical Formula2-A:

in Chemical Formula 2-A, Ar11 and Ar12 are the same as or different fromeach other, and are each independently a substituted or unsubstitutedmonocyclic aryl group; or a substituted or unsubstituted polycyclic arylgroup, and G1 to G8 are the same as or different from each other, andare each independently hydrogen; a substituted or unsubstitutedmonocyclic aryl group; or a substituted or unsubstituted polycyclic arylgroup.